Jerry Reinsdorf is a notoriously stingy owner. It plagues pretty much everything his Chicago White Sox do and is a big reason for the team's yearly struggles.
The White Sox are 25-53 in 2025, once again boasting the worst record in the American League by a wide margin. That means when the MLB trade deadline rolls around, the rebuilding White Sox will inevitably be sellers.
Unlike years past, the White Sox do not have a ton of high-end assets to deal at this year's deadline. Chicago will most likely be trading away rental veteran starting pitchers like Aaron Civale and Adrian Houser along with any relief pitchers that net a mediocre prospect return.
The big deadline question is what the White Sox will do with outfielders Andrew Benintendi and Luis Robert Jr.
Contracts will complicate the trade deadline
Robert Jr. has been in trade conversations for quite some time now, but his nightmare 2025 season has completely tanked his value.
Benintendi had a spectacular second half of the 2024 season and has been solid in 2025 (106 OPS+), but he is owed over $40 million over the next 2.5 years and I'm not sure there are teams motivated to trade away prospects and pay Benintendi $17.1 million next season.
You couldn't pay me to take Andrew Benintendi right now.
— Baseball is Everything (@ReportOnSports) June 20, 2025
Robert Jr. is owed over $10 million in the second half of the 2025 season. He has club control through 2027, but that would require his team to pick up $20 millIon club options each year. With the way he's playing, that's not going to happen...and if that's not going to happen, Robert Jr. is a rental outfielder that is struggling at the plate and not worth giving up legitimate prospects for.
The contract situations make it more difficult for Chris Getz to get valuable returns for both Robert Jr. and/or Benintendi. But it seems Jerry Reinsdorf is willing to do something out of character to help out his front office: Spend money!
Reinsdorf willing to spend?
According to reports from Ken Rosenthal and Will Sammon of The Athletic, the White Sox are willing to include cash in a trade to help pay for the salaries of their expensive outfielders.
In doing so, the White Sox hope that Benintendi and Robert will be easier to move and the return packages will start to get a little heavier.
It also can't hurt for the White Sox to get out of Benintendi's contract given the current state of the team. The five-year, $75 million deal is still the largest contract in Chicago White Sox history, which is sad.
It's a bit surprising, but albeit refreshing, to see the White Sox willing to make this kind of move. Jerry Reinsdorf has not been known to pay unnecessary dollars for players to play for other teams. He has only ever been worried about his bottom line. Perhaps this is a result of the Justin Ishbia cash infusions that are coming to the organization for the next five years.
Whatever the cause, I'm glad it's happening. If the Sox can maximize the returns on Benintendi and Robert at the deadline, it will bring them significantly closer to fielding a winning team in the future.
With young players like Miguel Vargas, Chase Meidroth, Kyle Teel, Shane Smith, Edgar Quero, and Grant Taylor in the Major Leagues, the White Sox are already establishing a decent foundation. Now they need to supplement it with as much young talent as possible.